2-arylcyclopentan-1,3-diones

ABSTRACT

The present invention relates to novel 2-aryl-3-hydroxy-Δ 2 -cyclopentene-1-one derivatives of the formula (I)                    
     in which 
     A, B, D 1 , D 2 , G, W, X, Y and Z are each as defined in the description, 
     to processes for their preparation and to their use as herbicides and pesticides.

This is the US National Stage Application of PCT/EP98/00916 filed Feb.18, 1998.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to novel2-aryl-3-hydroxy-Δ²-cyclopentene-1-one derivatives, to processes fortheir preparation and to their use as herbicides and pesticides.

BACKGROUND OF THE INVENTION

It is known that certain substituted 2-arylcyclopentane diones haveherbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos.4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547, 4,632,698, WO96/01798 and WO 96/03366). Moreover, compounds which are substituted ina similar manner are known;3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-ene-1-one from thepublication Micklefield et al., Tetrahedron, (1992), 7519-26 and thenatural compound involutin(−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enonefrom the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. Aninsecticidal or acaricidal action has not been described.

However, the acaricidal and insecticidal activity and/or activityspectrum, and the compatibility of these compounds with plants, inparticular crop plants, is not always satisfactory.

DETAILED DESCRIPTION OF THE INVENTION

This invention, accordingly, provides novel compounds of the formula (I)

in which

W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl,alkoxy, halogenalkyl, halogenalkoxy, in each case optionally substitutedphenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,

X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy,halogenalkyl, halogenoalkoxy, cyano, nitro, in each case optionallysubstituted phenyl, phenylalkyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio, with the proviso that at least one of the substituentsW and X does not represent hydrogen,

Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro,

Z represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy,hydroxyl, cyano, nitro or in each case optionally substituted phenoxy,phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio,phenylalkyloxy or phenylalkylthio, or

Y and Z together with the carbon atoms to which they are attachedrepresent an optionally substituted ring which is optionally interruptedby one or more heteroatoms, where X and W have one of the meaningsmentioned above, or

W and Z together with the carbon atoms to which they are attachedrepresent an optionally substituted ring which is optionally interruptedby one or more heteroatoms, where X and Y have one of the meaningsmentioned above,

A represents hydrogen or represents alkyl, alkenyl, alkinyl,alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which isoptionally mono- or polysubstituted by identical or different halogens,represents saturated or unsaturated, unsubstituted or substitutedcycloalkyl which is optionally interrupted by one or more heteroatoms orrepresents phenyl or phenylalkyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cyano and nitro,

B represents alkyl or alkoxyalkyl,

or

A and B together with the carbon atom to which they are attached form asaturated or unsaturated, optionally substituted ring which isoptionally interrupted by one or more heteroatoms,

or

A and B together with the carbon atom to which they are attached form aring where two substituents together with the carbon atoms to which theyare attached form a saturated or unsaturated ring which is optionallymono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, alkyl and alkoxy and which may containoxygen or sulphur,

D¹ and D² independently of one another each represent hydrogen, halogen,optionally halogen-substituted alkyl or optionally substituted phenyl,

G represents hydrogen (a) or represents one of the groups

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, each of which is optionally mono- or polysubstituted byidentical or different halogens, or represents optionally substituted,saturated or unsaturated cycloalkyl which may be interrupted by one ormore heteroatoms, or represents in each case optionally substitutedphenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,

R² represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, each ofwhich is optionally mono- or polysubstituted by identical or differenthalogens, or represents in each case optionally substituted cycloalkyl,phenyl or benzyl,

R³ represents alkyl which is optionally mono- or polysubstituted byidentical or different halogens or represents in each case optionallysubstituted phenyl or phenylalkyl,

R⁴ and R⁵ independently of one another each represent alkyl, alkoxy,alkylamino, alkenylamino, dialkylamino, dialkenylamino, alkylthio,alkenylthio, alkinylthio, cycloalkylthio, each of which is optionallymono- or polysubstituted by identical or different halogens, orrepresents in each case optionally substituted phenyl, phenoxy orphenylthio,

R⁶ and R⁷ independently of one another each represent hydrogen,represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of whichis optionally mono- or polysubstituted by identical or differenthalogens, or represent optionally substituted phenyl or optionallysubstituted benzyl,

or together with the N atom to which they are attached form anoptionally substituted ring which optionally contains oxygen or sulphur,

and the enantiomerically pure forms of compounds of the formula (I).

Depending, inter alia, on the nature of the substituents, the compoundsof the formula (I) can be present as geometrical and/or optical isomersor isomer mixtures of different composition which are separated, ifappropriate, in a customary manner by physical methods, for example bychromatographic methods.

Depending on the position of the substituent G, the compounds of theformula (I) can be present in the two isomeric forms of the formulae I-Aand -B

which is meant to be expressed by the dotted line in the formula (I).

The compounds of the formulae I-A and I-B can be present both asmixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae I-A and I-B may optionally be separated byphysical methods, for example by chromatographic methods.

For reasons of clarity, hereinbelow only one of the possible isomers isshown in each case. It is implied that the compound in question may bepresent as a mixture of isomers or in the respective other isomericform.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (Ia) to (Ig) result:

in which

A, B, D¹, D², E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

Furthermore, it has been found

(A) that compounds of the formula (IA)

in which

A, B, D¹, D², W, X, Y and Z are each as defined above

are obtained when

ketocarboxylic esters of the formula (II)

in which

A, B, D¹, D², W, X, Y and Z are each as defined above and

R⁸ represents alkyl (in particular C₁-C₈-alkyl)

are cyclized intramolecularly, if appropriate in the presence of adiluent and in the presence of a base, and

(B) that the compounds of the formula (Ib) shown above, in which A, B,D¹, D², R¹, W, X, Y and Z are each as defined above, are obtained whencompounds of the formula (Ia) shown above, in which A, B, D¹, D², W, X,Y and Z are each as defined above are reacted

α) with acyl halides of the formula (III)

in which

R¹ is as defined above and

Hal represents halogen (in particular chlorine or bromine)

or

β) with carboxylic anhydrides of the formula (IV)

R¹—CO—O—CO—R¹  (IV)

in which

R¹ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(C) that the compounds of the formula (Ic) shown above, in which A, B,D¹, D², R², W, M, X, Y and Z are each as defined above and L representsoxygen, are obtained when compounds of the formula (Ia) shown above, inwhich A, B, D¹, D², W, X, Y and Z are each as defined above, are reactedwith chloroformic esters or chloroformic thioesters of the formula (V)

R²—M—CO—Cl  (V)

in which

R² and M are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(D) that compounds of the formula (Ic) shown above, in which A, B, D¹,D², R², W, M, X, Y and Z are each as defined above and L representssulphur, are obtained when compounds of the formula (la) shown above, inwhich A, B, D¹, D², W, X, Y and Z are each as defined above, are reactedwith chloromonothioformic esters or chlordithioformic esters of theformula (VI)

in which

M and R² are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

or

(E) that compounds of the formula (Id) shown above, in which A, B, D¹,D², R³, W, X, Y and Z are each as defined above, are obtained whencompounds of the formula (Ia) shown above, in which A, B, D¹, D², W, X,Y and Z are each as defined above, are reacted

with sulphonyl chlorides of the formula (VII)

R³—SO₂—Cl  (VII)

in which

R³ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(F) that compounds of the formula (Ie) shown above, in which A, B, D¹,D², L, R⁴, R⁵, W, X, Y and Z are each as defined above, are obtainedwhen compounds of the formula (Ia) shown above, in which A, B, D¹, D²,W, X, Y and Z are each as defined above, are reacted

with phosphorus compounds of the formula (VIII)

in which

L, R⁴ and R⁵ are each as defined above and

Hal represents halogen (in particular chlorine or bromine),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(G) that compounds of the formula (I1) shown above, in which A, B, D¹,D², L, R⁶, R⁷, W, X, Y and Z are each as defined above, are obtainedwhen compounds of the formula (Ia) shown above, in which A, B, D¹, D²,W, X, Y and Z are each as defined above, are in each case reacted

α) with isocyanates or isothiocyanates of the formula (XI)

R⁶—N═C═L  (XI)

in which

R⁶ and L are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or

β) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula(XII)

in which

L, R⁶ and R⁷ are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(H) that compounds of the formula (Ig) shown above, in which A, B, D¹,D², E, W, X, Y and Z are each as defined above, are obtained whencompounds of the formula (Ia), in which A, B, D¹, D², W, X, Y and Z areeach as defined above, are reacted

with metal compounds or amines of the formula (IX) or (X)

in which

Me represents a mono- or divalent metal (preferably an alkali metal oralkaline earth metal such as lithium, sodium, potassium, magnesium orcalcium),

t represents the number 1 or 2 and

R¹⁰, R¹¹, R¹² independently of one another each represent hydrogen oralkyl (preferably C₁-C₈-alkyl),

if appropriate in the presence of a diluent.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticidesand acaricides and, at higher application rates, also as herbicides andare additionally tolerated very well by plants, in particular by cropplants.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned hereinabove and hereinbelow areillustrated below:

W preferably represents hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl orC₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,nitro, cyano or m each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio,

X preferably represents hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano, nitro or in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenylthio,phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio, with the proviso that atleast one of the substituents W and X does not represent hydrogen.

Y preferably represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

Z preferably represents halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl, cyano, nitro or ineach case optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenoxy, phenylthio, thiazolyloxy, pyridinyloxy,pyrimidinyloxy, pyrazolyloxy, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio, or

Y and Z together preferably represent in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl in which optionally one to threemembers may be replaced independently of one another by oxygen, sulphur,nitrogen or a carbonyl group, where X and W have one of the meaningsmentioned above, or

W and Z together preferably represent in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl in which optionally one to threemembers may be replaced independently of one another by oxygen, sulphur,nitrogen or a carbonyl group, where X and Y have one of the meaningsmentioned above.

A preferably represents hydrogen, represents in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl orC₁-C₁₀-alkylthio-C₁-C₆-alkyl, represents in each case optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur or represents in each case optionallyhalogen-, C₁-C₆-alkyl/C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl orphenyl-C₁-C₆-alkyl.

B preferably represents C₁-C₁₂-alkyl or C₁-C₈-alkoxy-C₁-C₆-alkyl or

A, B and the carbon atom to which they are attached preferably representC₃-C₁₀-cycloalkyl or C₅-C₁₀-cycloalkenyl in which optionally onemethylene group is replaced by oxygen or sulphur and which areoptionally substituted by C₁-C₈-alkyl, C₃-C₁₀-cycloalkyl,C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl,or

A, B and the carbon atom to which they are attached preferably representC₅-C₆-cycloalkyl which is optionally substituted by an alkylenediyl orby an alkylenedioxyl or by an alkylenedithioyl group which optionallycontains one or two not directly adjacent oxygen and/or sulphur atomswhich, with the carbon atom to which it is attached, forms a furtherfive- to eight-membered ring, or

A, B and the carbon atom to which they are attached preferably representC₃-C₈cycloalkyl or C₅-C₈-cycloalkenyl in which two carbon atoms arelinked with one another by C₃-C₆-alkanediyl, C₃-C₆-alkenediyl orC₄-C₆-alkanediendiyl, each of which is optionally substituted byC₁-C₆-alkyl, C₁-C₆-alkoxy or halogen, in which in each case optionallyone methylene group is replaced by oxygen or sulphur.

D¹ and D² independently of one another each preferably representhydrogen, halogen, C₁-C₆-alkyl which is optionally mono- orpolysubstituted by identical or different halogens or represent phenylwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, nitro, C₁-C₆-halogenoalkyl or C₁-C₆-halogenoalkoxy.

G preferably represents hydrogen (a) or represents one of the groups

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ preferably represents in each case optionally halogen-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₈-alkylthio-C₁-C₈-alkyl or poly-C₁-C₈-alkoxy-C₁-C₈-alkyl orrepresents optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur,

represents optionally halogen-, cyano-, nitro, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,

represents optionally halogen-, nitro, cyano, C₁-C₆-alkyl, C₁ C₆-alkoxy,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl having one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, for example pyrazolyl,thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,

represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

represents optionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryloxy-C₁-C₆-alkyl having one or two heteroatoms from thegroup consisting of oxygen, sulphur and nitrogen, for examplepyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyly orthiazolyloxy-C₁-C₆-alkyl.

R² preferably represents in each case optionally halogen-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

represents optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl or

represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl.

R³ preferably represents optionally halogen-substituted C₁ -C₈-alkyl orin each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- or nitro-substitutedphenyl or benzyl.

R⁴ and R⁵ independently of one another each preferably represent in eachcase optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈-alkenylthio or

represent in each case optionally halogen-, nitro-, cyano-,C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenoalkylthio, C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substitutedphenyl, phenoxy or phenylthio.

R⁶ and R⁷ independently of one another each preferably representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl orC₁-C₈-alkoxy-C₂-C₈-alkyl, represent in each case optionally halogen-,C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or C₁-C₈-alkoxy-substituted phenyl orbenzyl or together represent an optionally C₁-C₆-alkyl-substitutedC₃-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.

W particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro, cyano or in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy orbenzyloxy.

X particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano, nitro or in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,benzyl or benzyloxy, with the proviso that at least one of thesubstituents W and X does not represent hydrogen.

Y particularly preferably represents hydrogen, fluorine, chlorine,bromine C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro.

Z particularly preferably represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,hydroxyl, cyano, nitro or in each case optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenoxy or benzyloxy,or

Y and Z together particularly preferably represent optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃C₄-alkanediyl in which optionally oneor two not directly adjacent members may be replaced independently ofone another by oxygen, sulphur or nitrogen, or representC₃-C₄-alkenediyl in which optionally one member is replaced by oxygen,sulphur or nitrogen, where X and W have one of the meanings mentionedabove, or

W and Z together particularly preferably represent in each caseoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl in which one or twonot directly adjacent members may be replaced independently of oneanother by oxygen, sulphur or nitrogen, or represent C₃-C₄-alkenediyl inwhich optionally one member is replaced by oxygen, sulphur or nitrogen,where X and Y have one of the meanings mentioned above.

A particularly preferably represents hydrogen, represents in each caseoptionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₁-C₈-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkylor C₁-C₈-alkylthio-C₁-C₆-alkyl or represent optionally fluorine-,chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur or represent in each case optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenylor phenyl-C₁-C₄-alkyl,

B particularly preferably represents C₁-C₁₀-alkyl orC₁-C₆-alkoxy-C₁-C₄-alkyl or

A, B and the carbon atom to which they are attached particularlypreferably represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which ineach case optionally one methylene group is replaced by oxygen orsulphur and which are optionally substituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,fluorine, chlorine or phenyl, or

A, B and the carbon atom to which they are attached particularlypreferably represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl or by an alkylenedioxyl or by an alkylenedithio group groupwhich optionally contains one or two not directly adjacent oxygen orsulphur atoms which, with the carbon atom to which it is attached, formsa further five- to seven-membered ring, or

A, B and the carbon atom to which they are attached particularlypreferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twocarbon atoms are linked by in each case optionally C₁-C₄-alkyl-,C₁-C₄-alkoxy-, fluorine-, chlorine- or bromine-substitutedC₃-C₅-alkanediyl, C₃-C₅-alkenediyl, where in each case optionally onemethylene group is replaced by oxygen or sulphur, or by butadienediyl.

D¹ and D² independently of one another each preferably representhydrogen or particularly preferably represent C₁-C₄-alkyl which isoptionally mono- to pentasubstituted by identical or differentsubstituents from the group consisting of fluorine and chlorine.

G particularly preferably represents hydrogen (a) or represents one ofthe groups

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ particularly represents in each case optionally fluorine- orchlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆alkylthio-C₁-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₁-C₆-alkyl or represents optionally fluorine-,chlorine- C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur,

represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,

represents optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl-C₁-C₄-alkyl,

represents in each case optionally fluorine-, chlorine- bromine- orC₁-C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl,furanyl or thienyl,

represents optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl or

represents in each case optionally fluorine-, chlorine-, bromine-,amino- or C₁-C₄-alkyl-substituted pyridyloxy-C₁-C₅-alkyl,pyrimidyloxy-C₁-C₅-alkyl or thiazolyloxy-C₁-C₅-alkyl.

R² particularly preferably represents in each case optionally fluorine-or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,

represents optionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄alkoxy-substituted C₃-C₇-cycloalkyl or

represents in each case optionally fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl or benzyl.

R³ particularly preferably represents optionally fluorine- orchlorine-substituted C₁-C₆-alkyl or represents in each case optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkoxy-, C₁-C₂-halogenoalkyl-, cyano or nitro-substitutedphenyl or benzyl.

R⁴ and R⁵ independently of one another each particularly preferablyrepresent in each case optionally fluorine- or chlorine-substitutedC₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino,C₁-C₆-alkylthio or C₃-C₄-alkenylthio or represent in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-,C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl- orC₁-C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio.

R⁶ and R⁷ independently of one another each particularly preferablyrepresent hydrogen, represent in each case optionally fluorine- orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, represent in each caseoptionally fluorine-, chlorine-, bromine-, C₁-C₅-halogenoalkyl-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted phenyl or benzyl, or togetherrepresent an optionally C₁-C₄-alkyl-substituted C₃-C₆-alkylene radicalin which optionally one methylene group is replaced by oxygen orsulphur.

W very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl,tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano, nitro, phenyl or benzyloxy.

X very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, n-propyl, n-butyl, iso-butyl, iso-propyl,tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy,with the proviso that at least one of the substituents W and X does notrepresent hydrogen.

Y very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl,tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro,

Z very particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, n-propyl, n-butyl, iso-butyl, iso-propyl, tert-butyl,methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro, or

Y and Z together very particularly preferably represent optionallyfluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-,ethoxy-, n-propoxy-, iso-propoxy- or trifluoromethyl-substitutedC₃-C₄-alkanediyl in which optionally two not directly adjacent membersare replaced by oxygen, where W and X have one of the meanings mentionedabove, or

W and Z together very particularly preferably represent optionallyfluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-,ethoxy-, n-propoxy-, iso-propoxy- or trifluoromethyl-substitutedC₃-C₄-alkanediyl in which optionally two not directly adjacent membersare replaced by oxygen, where X and Y have one of the meanings mentionedabove.

A very particularly preferably represents hydrogen, represents in eachcase optionally fluorine- or chlorine-substituted C₁-C₈-alkyl,C₃-C₄-alkenyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkylor C₁-C₆-alkylthio-C₁-C₄-alkyl or represents optionally fluorine-,chlorine-, methyl- or methoxy-substituted C₃-C₆-cycloalkyl in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur or represents in each case optionallyfluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, iso-propyl-,methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl.

B very particularly preferably represents C₁-C₈-alkyl orC₁-C₄-alkoxy-C₁-C₂-alkyl or

A, B and the carbon atom to which they are attached very particularlypreferably represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which ineach case optionally one methylene group is replaced by oxygen orsulphur and which are optionally substituted by methyl, ethyl, n-propyl,iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl,trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy,iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine,chlorine or phenyl.

D¹ and D² independently of one another each very particularly preferablyrepresent hydrogen, methyl or ethyl.

G very particularly preferably represents hydrogen (a) or represents oneof the groups

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ very particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C ₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl orpoly-C₁-C₄-alkoxy-C₁-C₄-alkyl or represents optionally fluorine-,chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-,tert-butyl-, methoxy-, ethoxy-, n-propoxy- or iso-propoxy-substitutedC₃-C₆-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur,

represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-,methylsulphonyl- or ethylsulphonyl-substituted phenyl,

represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted benzyl,

represents in each case optionally fluorine-, chlorine-, bromine-,methyl- or ethyl-substituted furanyl, thienyl or pyridyl,

represents optionally fluorine-, chlorine-, methyl- or ethyl-substitutedphenoxy-C₁-C₄-alkyl or

represents in each case optionally fluorine-, chlorine-, amino-, methyl-or ethyl-substituted pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl.

R² very particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl,

represents optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,iso-propyl- or methoxy-substituted C₃-C₆-cycloalkyl,

or represents in each case optionally fluorine-, chlorine-, cyano-nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl.

R³ very particularly preferably represents optionally fluorine- orchlorine-substituted methyl, ethyl, n-propyl, iso-propyl, n-butyl,tert-butyl or in each case optionally fluorine-, chlorine-, bromine-,methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, ethoxy-,iso-propoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl.

R⁴ and R⁵ independently of one another each very particularly preferablyrepresent in each case optionally fluorine- or chlorine-substitutedC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino orC₁-C₄-alkylthio or represent in each case optionally fluorine-,chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-, trifluoromethyl-or trifluoromethoxy-substituted phenyl, phenoxy or phenylthio.

R⁶ and R⁷ independently of one another each very particularly preferablyrepresent hydrogen, represent in each case optionally fluorine- orchlorine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, represent in each caseoptionally fluorine-, chlorine-, bromine-, methyl-, methoxy- ortrifluoromethyl-substituted phenyl or benzyl or together represent anoptionally methyl- or ethyl-substituted C₅-C₆-alkylene radical in whichoptionally one methylene group is replaced by oxygen or sulphur.

The abovementioned general or preferred radical definitions orillustrations can be combined with one another as desired, i.e.including combinations between the ranges and preferred ranges inquestion. They apply both to the end product and, correspondingly, tothe precursors and intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

A preferred group of compounds of the formula (I) are those compounds inwhich D¹ and D² represent hydrogen.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as is possible,including in combination with heteroatoms, such as, for example, inalkoxy.

Optionally substituted radicals may be mono- or polysubstituted, and, inthe case of polysubstitions, the substituents may be identical ordifferent.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be mentionedspecifically:

TABLE 1

W = CH₃; X = CH₃; Y = CH₃; Z = CH₃ A B CH₃ CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉ CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —CH₂—O—(CH₂)₃——(CH₂)₂—S—(CH₂)₂— —CH₂—O—(CH₂)₃— —CH₂—CHCH₃—(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— —(CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂——(CH₂)₂—CHi-C₃H₇—(CH₂)₂— —(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂——(CH₂)₂—CHOC₃H₇—(CH₂)₂— —(CH₂)₂—CHOi-C₃H₇—(CH₂)₂——(CH₂)₂—C(CH₃)₂—(CH₂)₂— —CH₂—(CHCH₃)₂—(CH₂)₂—

Table 2

A and B are as defined in Table 1, and

W=CH₃; X=CH₃; Y=H; Z=Cl

Table 3

A and B are as defined in Table 1 and

W=CH₃; X=CH₃; Y=CH₃; Z=F

Table

A and B are as defined in Table 1 and

W=CH₃; X=CH₃; Y=CH₃; Z=Cl

Table 5

A and B are as defined in Table 1 and

W=CH₃; X=CH₃; Y=CH₃; Z=Br

Table 6

A and B are as defined in Table 1 and

W=CH₃; X=CH₃; Y=H; Z=Br

Table 7

A and B are as defined in Table 1 and

W=Cl; X=Cl; Y=H; Z=Br

Table 8

A and B are as defined in Table 1 and

W=Br, X=Br; Y, Z=—(CH₂)₃—

Table 9

A and B are as defined in Table 1 and

W=CH₃; X=OCH₃; Y=H; Z=Br

Table 10

A and B are as defined in Table 1 and

W=CH₃; X=CH₃; Y=CH₃; Z=CH₃

Table 11

A and B are as defined in Table 1 and

W=Cl; X=Cl; Y=Cl; Z=CH₃

Table 12

A and B are as defined in Table 1 and

W=Br; X=Br; Y=Br; Z=CH₃

Table 13

A and B are as defined in Table 1 and

W=H; X=Cl; Y=Cl; Z=Cl

Table 14

A and B are as defined in Table 1 and

W=H; X=CH₃; Y=CH₃, Z=CH₃

Table 15

A and B are as defined in Table 1 and

W=H, X=CH₃; Y=Cl, Z=CH₃

Table 16

A and B are as defined in Table 1 and

W=H; X=Br, Y=CH₃; Z=Cl

Table 17

A and B are as defined in Table 1 and

W=H; X=Br; Y=CH₃; Z=CH₃

Table 18

A and B are as defined in Table 1 and

W=H; X=Cl; Y=Br, Z=CH₃

Table 19

A and B are as defined in Table 1 and

W=H; X=Cl; Y=Cl; Z=CH₃

Table 20

A and B are as defined in Table 1 and

W=H; X=CH₃; Y=CH₃; Z=Br

Table 21

A and B are as defined in Table 1 and

W=H; X=Cl; Y, Z=—CF₂—O—

Table 22

A and B are as defined in Table 1 and

W=H; X=Br; Y=CH₃; Z=Br

Table 23

A and B are as defined in Table 1 and

W=H; X=CH₃; Y=H; Z=CH₃

Table 24

A and B are as defined in Table 1 and

W=H; X=Cl; Y=H; Z=NO₂

Table 25

A and B are as defined in Table 1 and

W=H; X=Br; Y=H; Z=OCH₃

Using according to Process (A) ethyl5-(2,4,6-trichloro-3-methylphenyl)-2,2-dimethyl-4-oxo-valerate asstarting material, the course of the process according to the inventioncan be represented by the following reaction scheme:

Using according to process (B) (variant α)2-(2,4,6-trimethyl-3-chlorophenyl)-3-hydroxy-4,4-dimethyl-Δ²-cyclopentenoneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using according to process (B) (variant β)2-(2,5-dimethylphenyl)-3-hydroxy-4-methyl-4-phenyl-Δ²-cyclopentenone andacetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using according to process (C)2-(2,4-dichlor-5-methylphenyl)-3-hydroxy-4-isopropyl-4-methyl-Δ²-cyclopentenoneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

Using according to process (D)2-(2,4,5-trimethylphenyl)-3-hydroxy-4-ethyl-4-methyl-Δ²-cyclopentenoneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using according to process (E)2-(2,4,6trimethyl-3-bromophenyl)-3-hydroxy-4,4-(4-methoxy)-pentamethylene-Δ²-cyclopentenoneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following reaction scheme:

Using according to process (F)2-(2,4,5-trimethylphenyl)-3-hydroxy-4,4-dimethyl-Δ²-cyclopentenone and2,2,2-trifluoroethyl methanethio-phosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing reaction scheme:

Using according to process (Gα)2-(2,6-dimethyl-3-bromophenyl)-3-hydroxy-4,4-tetramethylene-Δ²-cyclopentenoneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following reaction scheme:

Using according to process (Gβ)2-(2,3,4,6-tetramethylphenyl)-3-hydroxy-4-trifluoromethylmethyl-Δ²-cyclopentenoneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

Using according to process (H)2-(2,4,6-trimethyl-3-fluorophenyl)-3-hydroxy-4,4-dimethyl-Δ²-cyclopentenoneand NAOH as components, the course of the process according to theinvention can be represented by the following reaction scheme:

The compounds of the formula (II)

in which

A, B, D¹, D², W, X, Y, Z, n and R⁸ are each as defined above,

which are required as starting materials for the process (A) above

are novel.

They can be prepared by methods known in principle.

The 5-aryl-4-ketocarboxylic esters of the formula (II) are obtained, forexample, when 5-aryl-4-ketocarboxylic acids of the formula (XIII)

in which

W, X, Y, Z, A, B, D¹ and D² are each as defined above are esterified(cf., for example, Organikum, 15th Edition, Berlin, 1977, page 499) oralkylated (see Preparation Example).

The 5-aryl-4-ketocarboxylic acids of the formula (XIII)

in which

A, B, D¹, D², W, X, Y and Z are each as defined above

are novel; however, they can be prepared by methods known in principle(see Preparation Example)

The 5-aryl-4-ketocarboxylic acids of the formula (XIII) are obtained,for example, when carboxylic anhydrides of the formula (XIV)

in which

A, B, D¹ and D² are each as defined above,

are reacted with organometallic compounds of the formula (XV)

in which

W, X, Y and Z are each as defined above,

Met represents mono- or divalent metal ions, for example those oflithium or magnesium,

Hal represents chlorine or bromine

and

l represents a number 0 or 1

in the presence of a diluent (cf., for example, Organikum, 15th Edition,Berlin, 1977, page 623).

Some of the compounds of the formulae (XIV) and (XV) are known, and/orthey can be prepared by known processes (cf., for example, Organikum,15th Edition, Berlin, 1977, pages 525, 526 and 623).

Furthermore, 5-aryl-4-ketocarboxylic acids of the formula (XIII)

in which

A, B, D¹, D², W, X, Y and Z are each as defined above,

are obtained when 2-phenyl-3-oxo-adipates of the formula (XVI)

in which

A, B, D¹, D², W, X, Y and Z are each as defined above and

R⁸ and R^(8′) represent alkyl (in particular C₁-C₈-alkyl)

are decarboxylated, if appropriate in the presence of a diluent and ifappropriate in the presence of a base or an acid (cf., for example,Organikum, 15th Edition, Berlin, 1977, pages 519 to 521)

The compounds of the formula (XVI)

in which

A, B, D¹, D², W, X, Y, Z, R⁸, R^(8′) are each as defined above

are novel.

The compounds of the formula (XVI) are obtained, for example,

when dicarboxylic monoester chlorides of the formula (XVII)

in which

A, B, D¹, D² and R⁸ are each as defined above and

Hal represents chlorine or bromine

or carboxylic anhydrides of the formula (XIV)

are acylated with a phenyl acetic ester of the formula (XVIII)

in which

W, X, Y, Z and R^(8′) are each as defined above

in the presence of a diluent and in the presence of a base (cf., forexample, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc.Chem. Commun., (1987), 1228, cf. also the Preparation Examples).

Some of the compounds of the formulae (XVII) are known compounds oforganic chemistry, and/or they can be prepared in a simple manner bymethods known in principle.

Some of the compounds of the formula (XVIII) are known (WO 97/36868, DE196 31 586, WO 97/01535, DE 19 02 524) or they can be prepared by theprocess described therein.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D¹, D², W, X, Y, Z and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

Suitable diluents for the process (A) according to the invention are allorganic solvents which are inert towards the reaction participants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone. It is furthermore possible to employ alcohols,such as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, calciumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which may also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl (C₈-C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). Furthermore, it is possible to usealkali metals, such as sodium or potassium. Moreover, alkali metal andalkaline earth metal amides and hydrides, such as sodium amide, sodiumhydride and calcium hydride, and moreover also alkali metal alkoxides,such as sodium methoxide, sodium ethoxide and potassium tert-butoxide,may be used.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −75° C. and250° C., preferably between −50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in approximately equimolar amounts However, it isalso possible to use a relatively large excess (up to 3 mol) of one orthe other component.

The process (Bα) is characterized in that compounds of the formula (Ia)are reacted with carbonyl halides of the formula (III), if appropriatein the presence of a diluent and if appropriate in the presence of anacid binder.

Suitable diluents for the process (Bα) according to the invention areall solvents which are inert towards the acyl halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such asdimethylformamide, dimethyl sulphoxide and sulpholane. The stability ofthe acyl halide hydrolysis permitting, it is also possible to carry outthe reaction in the presence of water.

Suitable acid binders for the reaction according to the process (Bα)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

When carrying out the process (Bα) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (Bα) according to the invention, thestarting materials of the formula (Ia) and the carbonyl halide of theformula (III) are generally employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(for example up to 5 mol) of the carbonyl halide. Work-up is carried outby customary methods.

The process (Bβ) is characterized in that compounds of the formula (Ia)are reacted with carboxylic anhydrides of the formula (IV), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for the process (Bβ) according to the invention arepreferably those diluents which are also preferred when acyl halides areused. Besides, it is also possible for a carboxylic anhydride employedin excess to act simultaneously as diluents.

In the process (Bβ), preferred acid binders, which are added ifappropriate, are those acid binders which are also preferred when acylhalides are used.

When carrying out the process (Bβ) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (Bβ) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (IV) are generally employed in approximately equivalentamounts. However, it is also possible to employ a relatively largeexcess (up to 5 mol) of the carboxylic anhydride. Work-up is carried outby customary methods.

In general, a procedure is used in which diluent and excess carboxylicanhydride and the resulting carboxylic acid are removed by distillationor by washing with an organic solvent or with water.

The process (C) is characterized in that compounds of the formula (I-a)are reacted with chloroformic esters or chloroformic thioesters of theformula (V), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable acid binders for the process (C) according to the invention areall customary acid acceptors. Preference is given to using tertiaryamines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hünig base andN,N-dimethylaniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, additionally alkali metal andalkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides, suchas sodium hydroxide and potassium hydroxide.

Suitable diluents for the process (C) according to the invention are allsolvents which are inert towards the chloroformic esters or chloroformicthioesters. Preference is given to using hydrocarbons, such as benzine,benzene, toluene, xylene and tetralin, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, moreover nitrites, such as acetonitrile,and also strongly polar solvents, such as dimethylformamide, dimethylsulphoxide and sulpholane.

When carrying out the process (C) according to the invention, thereaction temperature can be varied within a relatively wide range. Thereaction temperature is generally between −20° C. and +100° C.,preferably between 0° C. and 50° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (V) are generally in eachcase employed in approximately equivalent amounts. However, it is alsopossible to employ a relatively large excess (for example up to 2 mol)of one or the other components. Work-up is carried out by customarymethods. In general, a procedure is used in which precipitated salts areremoved and the reaction mixture which remains is concentrated bystripping off the diluent.

The process (D) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with compounds of the formula(VI) in the presence of a diluent and, if appropriate, in the presenceof an acid binder.

In the preparation process (D), approximately 1 Mol ofchloromonothioformic ester or chlorodithioformic ester of the formula(VI) is employed per mole of starting material of the formula (I-a), atfrom 0 to 120° C., preferably from 20 to 60° C.

Diluents which may be added, if appropriate, are all inert polar organicsolvents, such as ethers, amides, sulphones, sulphoxides, and alsohalogenoalkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders can be dispensed with.

If acid binders are used, customary inorganic or organic bases aresuitable. Sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine may be mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with sulphonyl chlorides ofthe formula (VII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder. In the preparationprocess (E), approximately 1 mol of sulphonyl chloride of the formula(VII) is employed per mole of starting material of the formula (I-a), atfrom −20 to 150° C., preferably from 0 to 70° C.

The process (E) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents, such as ethers,amides, ketones, carboxylic esters, nitrites, sulphones, sulphoxides orhalogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound of theformula (I-a) is prepared by addition of strong deprotonating agents(such as, for example, sodium hydride or potassium tert-butoxide), thefurther addition of acid binders can be dispensed with.

If acid binders are used, customary inorganic or organic bases aresuitable. Sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine may be mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with phosphorus compounds ofthe formula (VIII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

In the preparation process (F), in order to obtain compounds of theformula (I-e), from 1 to 2, preferably from 1 to 1.3, mol of thephosphorus compound of the formula (VIII) are reacted per mole of thecompound (I-a), at temperatures between 40° C. and 150° C., preferablybetween −10 and 110° C.

The process (F) is preferably carried out in the presence of a diluentSuitable diluents are all inert, polar organic solvents, such as ethers,carboxylic esters, halogenated hydrocarbons, ketones, amides, nitriles,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

Acid binders which may be added, if appropriate, are customary inorganicor organic bases, such as hydroxides, carbonates or amines. Sodiumhydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods of organicchemistry. The end products are preferably purified by crystallization,chromatographic purification or by so-called “incipient distillation”,i.e. removal of the volatile components under reduced pressure.

The process (G) according to the invention is characterized in thatcompounds of the formula (I-a) are (Gα) reacted with compounds of theformula (XI), if appropriate in the presence of a diluent and ifappropriate in the presence of a catalyst, or (Gβ) reacted withcompounds of the formula (XII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In the preparation process (Gα), approximately 1 mol of isocyanate ofthe formula (XI) is reacted per mole of starting material of the formula(I-a), at from 0 to 100° C., preferably at from 20 to 50° C.

The process (Gα) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert organic solvents, such as aromatichydrocarbons, halogenated hydrocarbons, ethers, amides, nitrites,sulphones or sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds, such as, for example, dibutyltin dilaurate.

The process is preferably carried out under atmospheric pressure.

In the preparation process (Gβ), approximately 1 mol of carbamoylchloride of the formula (XII) is reacted per mole of starting materialof the formula (I-a), at from 0 to 150° C., preferably at from 20 to 70°C.

Diluents which may be added, if appropriate, are all inert polar organicsolvents, such as ethers, carboxylic esters, nitriles, ketones, amides,sulphones, sulphoxides or halogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, customary inorganic or organic bases aresuitable. Sodium hydroxide, sodium carbonate, potassium carbonate,triethylamine or pyridine may be mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (H) is characterized in that compounds of the formula (I-f)are in each case reacted with metal hydroxides or metal alkoxides of theformula (IX) or amines of the formula (X), if appropriate in thepresence of a diluent.

Preferred diluents for the process (H) according to the invention areethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, and also water. Theprocess (H) according to the invention is generally carried out underatmospheric pressure. The reaction temperature is generally between −20°C. and 100° C., preferably between 0° C. and 50° C.

The active compounds are suitable for controlling animal pests,preferably anthropodes and nematodes, in particular insects andarachnids, encountered in agriculture, in forests, in the protection ofstored products and of materials, and in the hygiene sector. They areactive against normally sensitive and resistant species, and against allor some stages of development. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blatella gennanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregana.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphurn padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.

From the order of the lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthuiberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuelmiella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofinannophila pseudospretella,Cacoecia podana, Capua reticulana, Choristoneura flrnferana, Clysiaambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dorninica, Ancanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varive stis, Atomaria spp., Oxyzaephilussurinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera posfica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derusspp., Melolontha melolontha, Amphimallon solsti tialis and Costelytrazealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pbaraonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp, Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

In particular, the active compounds according to the invention haveexcellent insecticidal and acaricidal activity.

They can be used particularly successfully for controllingplant-damaging insects, for example against the larvae of the mustardbeetle (Phaedon cochleariae) or against the larvae of the green riceleaf hopper (Nephotettix cincticeps) or against caterpillars of thediamond back moth (Plutella maculipennis).

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, haulm-killers and, especially, asweedkillers. By weeds, in the broadest sense, are to be understood allplants which grow in locations where they are unwanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The dosages of the active compounds according to the invention requiredfor controlling weeds are between 0.001 and 10 kg/ha, preferably between0.005 and 5 kg/ha.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Sachharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

The active compounds according to the invention are highly suitable forthe selective control of monocotyledonous weeds in dicotyledonous cropsby both the pre- and the post-emergence method. They can be employedvery successfully for controlling harmful grasses for example in cottonor sugar beet.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspoemulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol and their ethers and esters, ketones, such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents, such as dimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates,suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite and synthetic granules of inorganic and organic meals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifiers and/or foam-formers are: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates andprotein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Possible furtheradditives are mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms.

Examples of particularly advantageous mixture components are thefollowing compounds:

Fungicides:

2-aminobutane; 2-anilino4-methyl-6cyclopropyl-pyrimidine;2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino-[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazirn, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferirnzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulphamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane, kasugamycin, copper preparations such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulphocarb, methfuroxam, metiram, metsulphovax,myclobutanil, nickel dimethyldithiocarbamate, nitrothal-isopropyl,nuarimol, ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin,piperalin, polycarbamate, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon, quintozene (PCNB),

sulphur and sulphur preparations,

tebucanozole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumnizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin. Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mevinphos, mesulphenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyradaphenthion, pyresmetirin, pyretirum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulphotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamnidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:

for example anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D,2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr,aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimeihalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenz-thiazuron;hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim,sethoxydim and tralkoxydim; imidazolinones such as, for example,imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as,for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as,for example, mefenacet; sulphonylureas such as, for example,amidosulphuron, bensulphuron-methyl, chlorimuron-ethyl, chlorsulphuron,cinosulphuron, metsulphuron-methyl, nicosulphuron, primisulphuron,pyrazosulphuron-ethyl, thifensulphuron-methyl, triasulphuron andtribenuron-methyl; thiolcarbamates such as, for example, butylate,cycloate, di-allate, EPTC, esprocarb, molinate, prosulphocarb,thiobencarb and tri-allate; triazines such as, for example, atrazine,cyanazine, simazine, simetryne, terbutryne and terbutylazine;triazinones such as, for example, hexazinone, metamitron and metribuzin;others such as, for example, aminotriazole, benfuresate, bentazone,cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr,ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben,pyridate, quinchlorac, quinmerac, sulphosate and tridiphane

The active compound according to the invention can furthermore bepresent in its commercially available formulations and in the use formsprepared from these formulations, as a mixture with synergistic agentsSynergistic agents are compounds which increase the action of the activecompounds without it being necessary for the synergistic agent added tobe active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound has an excellent residual action on wood and clay and a goodstability to alkali on limed substrates.

The active compounds according to the invention are not only activeagainst plant, hygiene and stored-product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites),such as ixodid ticks, argasid ticks, scab mites, trombiculid mites,flies (stinging and sucking), parasitic fly larvae, lice, hair lice,bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp..

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp..

From the order Diptera and the sub-orders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp. and Melophagus spp.,

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp..

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp..

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp..

From the sub-class of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example Argas spp., Ornithodorus spp., Otabiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp..

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Octodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..

For example, they show an outstanding activity against Boophilusmicroplus.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which attack agriculturallivestock, such as, for example, cattle, sheep, goats, horses, pigs,donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,honey bees, other domestic animals, such as, for example, dogs, cats,cage birds, aquarium fish, and so-called experimental animals such as,for example, hamsters, guinea-pigs, rats and mice. By controlling thesearthropods, it is intended to reduce mortality and decreased performance(in meat, milk, wool, hides, eggs, honey and the like), so that moreeconomical and simpler animal husbandry is made possible by using theactive compounds according to the invention.

In the veterinary sector, the active compounds according to theinvention are used in a known manner by enteral administration, forexample in the form of tablets, capsules, drinks, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration, such as, for example, by means of injections(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal application, by dermal administration, forexample in the form of dipping or bathing, spraying, pouring-on andspotting-on, washing, dusting, and with the aid of shaped articles whichcomprise active compound, such as collars, ear tags, tail marks, limbbands, halters, marking devices and the like.

When administered to livestock, poultry, domestic animals and the like,the active compounds of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) which comprise the activecompounds in an amount of 1 to 80% by weight, either directly or afterdilution by a factor of 100 to 10,000, or they may be used in the formof a chemical bath.

Furthermore, it has been found that the compounds of the formula (I)according to the invention have a potent insecticidal action againstinsects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without any limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis,Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis,Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.,Dinoderus minutus.

Dermapterans, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotemnes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as

Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials such as, preferably, plastics, glues, sizes,paper and board, leather, wood and timber products, and paint.

The materials to be very particularly protected against attack byinsects are wood and timber products.

Wood and timber products which can be protected by the compositionaccording to the invention or mixtures comprising such a composition areto be understood as meaning, for example: construction timber, woodenbeams, railway sleepers, bridge components, jetties, wooden vehicles,boxes, pallets, containers, telephone poles, wood lagging, windows anddoors made of wood, plywood, particle board, joiner's articles, or woodproducts which, quite generally, are used in the construction of housesor in joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and wooden materials comprise the active compound according to theinvention at a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight

The amount of the compositions or concentrates employed depends on thespecies and the occurrence of the insects and on the medium. The optimumrate of application can be determined upon use in each case by testseries. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

The solvent and/or diluent used is an organochemical solvent or solventmixture and/or an oily or oil-type organochemical solvent or solventmixture of low volatility and/or a polar organochemical solvent orsolvent mixture and/or water and, if appropriate, an emulsifier and/orwetting agent.

Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Substances which are usedas such oily and oil-type solvents which have low volatility and areinsoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oil-containing solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

Substances which are advantageously used are mineral oils with a boilingrange of 170 to 220° C., white spirit with a boiling range of 170 to220° C., spindle oil with a boiling range of 250 to 350° C., petroleumor aromatics of boiling range of 160 to 280° C., essence of turpentineand the like.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspinde oil and/or monochloronaphthalene, preferablyx-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

According to a preferred embodiment, part of the organochemical solventor solvent mixture is replaced by an aliphatic polar organochemicalsolvent or solvent mixture. Substances which are preferably used arealiphatic organochemical solvents having hydroxyl and/or ester and/orether groups, such as, for example, glycol ethers, esters and the like.

The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin, such asindene/coumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Up to 10% by weight of bitumen orbituminous substances can also be used as binders. In addition,colorants, pigments, water repellents, odour-masking substances andinhibitors or anticorrosives known per se and the like can also beemployed.

The composition or the concentrate preferably comprises, in accordancewith the invention, at least one alkyd resin or modified alkyd resinand/or a drying vegetable oil as the organochemical binder. Preferablyused according to the invention are alkyd resins with an oil content ofover 45% by weight, preferably 50 to 68% by weight.

All or some of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate,the phosphoric esters, such as tributyl phosphate, the adipic esters,such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearateor amyl stearate, the oleates, such as butyl oleate, the glycerol ethersor relatively high-molecular-weight glycol ethers, glycerol esters andp-toluene-sulphonic esters.

Fixatives are chemically based on polyvinyl alkyl ethers, such as, forexample, polyvinyl methyl ether, or ketones, such as benzophenone orethylene benzophenone.

Also particularly suitable as a solvent or diluent is water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by large-scaleindustrial impregnation processes, for example vacuum, double-vacuum orpressure processes.

If appropriate, the ready-to-use compositions can additionally compriseother insecticides and, if appropriate, additionally one or morefungicides.

Suitable additional components which may be admixed are, preferably, theinsecticides and fungicides mentioned in WO 94129 268. The compoundsmentioned in that document are expressly part of the presentapplication.

Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorofluanide, tolylfluanide,3-iodo-2-propinyl-butyl carbamate, N octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example Ia-1

2.7 g (24 mmol) of potassium tert-butoxide are added to a solution ofthe compound according to Example II-1 (4.4 g, 16 mmol) in DMF (30 ml),and the mixture is stirred at 80° C. for 1 hour. With cooling using anice bath, the mixture is stirred into approximately 600 ml of 1 NHCl,and the solid is filtered off with suction and dried Crude yield: 4 g(100% of theory). M.p. 185-186° C.

Analogously, and/or in accordance with the general preparationprocedures, the compounds of the formula (la) listed in Table 27, whichare shown in the form of one of the possible isomers, were prepared.

TABLE 27 (Ia)

Table 28, Examples Ia Ex. No. A B W X Y Z m.p. ° C. Ia-2  —(CH₂)₅— H CH₃H CH₃  202 Ia-3  —(CH₂)₅— H CH₃ CH₃ CH₃  218 Ia-4  —(CH₂)₅— CH₃ CH₃ CH₃CH₃ >250 Ia-5  —(CH₂)₂—CHCH₃—(CH₂)₂— H CH₃ CH₃ CH₃ 212 Ia-6  —(CH₂)₄— HCH₃ H CH₃ 174-175 Ia-7  —(CH₂)₄— H CH₃ CH₃ CH₃ 162-164 Ia-8  —(CH₂)₅— HCH₃ Cl CH₃ 202-203 Ia-9  —(CH₂)₅— CH₃ H H CF₃ 217-218 Ia-10—(CH₂)₂—CHCH₃—(CH₂)₂— H Br CH₃ CH₃ 178-181 Ia-11 —(CH₂)₂—CHCH₃—(CH₂)₂— HCH₃ H CH₃ 196-198 Ia-12 —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ CH₃ CH₃ F 195-197Ia-13 —(CH₂)₃—CHCH₃—CH₂— H CH₃ H CH₃ 71-73 Ia-14 —(CH₂)₂—CHOCH₃—(CH₂)₂—H CH₃ H CH₃ 215-217 Ia-15 —(CH₂)₂—CHOCH₃—(CH₂)₂— H CH₃ Cl CH₃ 179-180Ia-16 —(CH₂)₂—CHOCH₃—(CH₂)₂— H CH₃ CH₃ CH₃ 186-188 Ia-17—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ CH₃ CH₃ CH₃ 233-235 Ia-18 —(CH₂)₂—O—(CH₂)₂— HBr CH₃ CH₃ 196-198 Ia-19 —(CH₂)₂—O—(CH₂)₂— H Cl H CH₂CH₃ 146-154 Ia-20—(CH₂)₂—O—(CH₂)₂— H CH₃ H CH₃ >215 Ia-21 —(CH₂)₂—O—(CH₂)₂— CH₃ CH₃ CH₃CH₃ >250

Example Ib-1

1.5 g (6.0 mmol) of the compound of Example Ia-1 are initially chargedin 20 ml of dry methylene chloride and admixed with 1.25 ml (9.0 mmol;1.5 eq) of triethylamine.

A solution of 1.16 ml (1.14 g, 9.0 mmol; 1.5 eq) of pivaloyl chloride in3 ml of dry methylene chloride is added dropwise with ice-cooling. Themixture is stirred at room temperature for 1 to 2 hours and washed twicewith 10% strength citric acid, and the combined aqueous acidic phasesare extracted with methylene chloride. The combined organic phases arewashed twice with 1 N NaOH and the aqueous alkaline phases are extractedwith methylene chloride. The combined organic phases are combined andconcentrated.

Yield: 1.90 g (96.00% of theory). M.p. 75-77° C.

Analogously, and/or in accordance with the general preparationprocedures, the compounds of the formula (Ib) listed in Table 28, whichare shown in the form of one of the possible isomers, were prepared.

TABLE 28 (Ib)

Table 28, Examples Ib Ex. No. W X Y Z A B R¹ m.p. ° C. Ib-2  H CH₃ H CH₃—(CH₂)₅— t-C₄H₉ 105 Ib-3  H CH₃ H CH₃ —(CH₂)₅— t-C₄H₉—CH₂ 110 Ib-4  HCH₃ CH₃ CH₃ —(CH₂)₅— t-C₄H₉ 108 Ib-5  H CH₃ CH₃ CH₃ —(CH₂)₅— i-C₃H₇  62Ib-6  H CH₃ CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— t-C₄H₉  92 Ib-7  H CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— C₂H₅—O—CH₂— 185 Ib-8  CH₃ CH₃ CH₃ CH₃ —(CH₂)₅—t-C₄H₉ 131-132 Ib-9  CH₃ CH₃ CH₃ CH₃ —(CH₂)₅— C₂H₅—O—CH₂— wax Ib-10 HCH₃ CH₃ CH₃ —(CH₂)₄— t-C₄H₉ 80-83 Ib-11 H CH₃ CH₃ CH₃ —(CH₂)₄—C₂H₅—O—CH₂— 137-141 Ib-12 H CH₃ Cl CH₃ —(CH₂)₅— t-C₄H₉ 123-126 Ib-13 CH₃H H CF₃ —(CH₂)₅— t-C₄H₉ 86-88 Ib-14 CH₃ H H CF₃ —(CH₂)₅— C₂H₅—O—CH₂— waxIb-15 H Br CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— t-C₄H₉ oil Ib-16 H CH₃ H CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— t-C₄H₉ oil Ib-17 H CH₃ H CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂—Cl—CH₂—C(CH₃)₂— wax Ib-18 CH₃ CH₃ CH₃ F —(CH₂)₂—CHCH₃—(CH₂)₂— t-C₄H₉ oilIb-19 H CH₃ H CH₃ —(CH₂)₃—CHCH₃—CH₂— t-C₄H₉ oil Ib-20 H CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉ oil Ib-21 H CH₃ Cl CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉ 116-118 Ib-22 H CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉ wax Ib-23 CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉ 125-130 Ib-24 H Br CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— t-C₄H₉ wax Ib-25 H Cl H CH₂CH₃ —(CH₂)₂—O—(CH₂)₂—t-C₄H₉ oil Ib-26 H CH₃ H CH₃ —(CH₂)₂—O—(CH₂)₂— t-C₄H₉ wax Ib-27 CH₃ CH₃CH₃ CH₃ —(CH₂)₂—O—(CH₂)₂— t-C₄H₉ 122-125 Ib-28 CH₃ CH₃ CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— i-C₃H₇ 88-90

Example Ic-1

1.5 g (6.0 mmol) of the compound of Example Ia-I are initially chargedin 20 ml of dry methylene chloride and admixed with 1.25 ml (9.0 mmol;1.5 eq) of triethylamine.

A solution of 1.17 ml (1.23 g, 9.0 mmol; 1.5 eq) of isobutylchloroformate in 3 ml of dry methylene chloride is added dropwise withice-cooling. The mixture is stirred at room temperature for 1 to 2hours.

Work-up is carried out as described under Example Ib- 1.

Yield: 2.00 g of oil. 97% of theory.

¹H NMR (400 MHz, CDCl₃): 0.9 (d, 6H, CH(CH₃)₂); 1.2 (s, 6H, CH(CH₃)₂);1.9 (m, 1H, CH(CH₃)₂); 2.1 (s, 3H, ArCH₃); 2.2 (d, 6H, 2×ArCH₃), 2.9 (s,2H, CH₂); 3.9 (d, 2H, OCH₂); 6.8; 7.0 (s, 2H, Ar—H).

Analogously, and/or in accordance with the general preparationprocedures, the compounds of the formula (Ic) listed in Table 29, whichare shown in the form of one of the possible isomers, were prepared.

TABLE 29 (Ic)

Ex. No. W X Y Z A B L M R² m.p. ° C. Ic-2 CH₃ H H CF₃ —(CH₂)₅— O Si-C₃H₇— 106-109 Ic-3 H CH₃ H CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— O S i-C₃H₇— oilIc-4 H CH₃ H CH₃ —(CH₂)₃—CHCH₃—CH₂— O S i-C₃H₇— oil Ic-5 CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— O O i-C₄H₉— 114-116

Example If-1

1.0 g (3.5 mmol) of the compound of Example Ia- I1 is initially chargedin 30 ml of dried ethyl acetate and mixed with 0.73 ml (5.2 mmol; 1.5eq) of triethylamine.

A solution of 0.53 ml (0.68 g; 4.6 mmol; 1.3 eq) ofmorpholine-N-carbonyl chloride in 5 ml of dry ethyl acetate is addeddropwise at room temperature. The mixture is heated under reflux for 4hours.

The mixture is concentrated using a rotary evaporator and taken up inmethylene chloride. The mixture is washed twice with 0.5 N NaOH. Theorganic phase is dried and concentrated.

Yield: 1.0 g (72% of theory) of oil.

¹H NMR (400 MHz, DMSO-d₆): 0.95 (d, 31, CHCH₃); 1.3-1.8 (m, 9H,cyclohexyl-H); 2.05 (s, 3H, ArCH₃); 2.25 (s, 3H, ArCH₃); 2.9 (s, 2H,CH₂); 3.2-3.8 (m, 8H, morpholine-H); 6.85 (s, 1H, Ar—H), 7.05 (d, 1H,Ar—H); 7.12 (d, 1H, Ar—H).

Example (II-1)

6.40 g (46.5 mmol) of potassium carbonate and 19.78 g (139.5 mmol) ofmethyl iodide are added to 12.2 g (46.5 mmol) of the compound of Example(XIII-1) (crude product) in 100 ml of absolute acetone, and the mixtureis stirred under reflux for 16 hours. The mixture is filtered and thefiltrate is concentrated under reduced pressure. The residue (11.9 g) ischromatographed over silica gel and methylene chloride/petroleum ether8/1 to 1/0.

Yield: 4.70 g (47% of theory), oil

¹H NMR (400 MHz, CDCl₃): 1.1 (s, 6H, C(CH₃)₂); 2.1 (s, 3H, ArCH₃); 2.2(s, 6H, 2×ArCH₃); 2.7 (s, 2H, CH(CMe₂); 3.5 (s, 2H, ArCH₂), 3.6 (s, 3H,OCH₃); 6.8/6.9 (s, 2H, 2×ArCH).

Analogously to Example (II-1), and/or in accordance with the generalpreparation procedures, the compounds of the formula (II) listed inTable 30 were prepared.

TABLE 30 (II)

Table 30, Examples II Ex. No. W X Y Z A B R8 m.p. ° C. II-2  H CH₃ H CH₃—(CH₂)₅— CH₃ oil II-3  H CH₃ CH₃ CH₃ —(CH₂)₅— CH₃ oil II-4  CH₃ CH₃ CH₃CH₃ —(CH₂)₅— CH₃ 85-86 II-5  H CH₃ CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ oilll-6  H CH₃ H CH₃ —(CH₂)₄— CH₃ oil II-7  H CH₃ CH₃ CH₃ —(CH₂)₄— CH₃ oilII-8  H CH₃ Cl CH₃ —(CH₂)₅— CH₃ oil II-9  CH₃ H H CF₃ —(CH₂)₅— CH₃ oilII-10 H Br CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ oil II-11 H CH₃ H CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ oil II-12 CH₃ CH₃ CH₃ F —(CH₂)₂—CHCH₃—(CH₂)₂—CH₃ oil II-13 H CH₃ H CH₃ —(CH₂)₃—CHCH₃—CH₂— CH₃ oil II-14 H CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ oil II-15 H CH₃ Cl CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂—CH₃ oil II-16 H CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ oil II-17 CH₃ CH₃CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ oil II-18 H Br CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— CH₃ oil II-19 H Cl H CH₂CH₃ —(CH₂)₂—O—(CH₂)₂— CH₃ oilII-20 H CH₃ H CH₃ —(CH₂)₂—O—(CH₂)₂— CH₃ oil II-21 CH₃ CH₃ CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— CH₃ oil

Example XII-1

A solution of 10.3 g (54 mmol; 1 eq) of methyl2,4,5-trimethyl-phenylacetate and 20 ml of tetrahydrofuran (THF) p.a. isadded dropwise, at −15° C., to a solution of 30.0 ml of LDA (lithiumdiisopropylamide) solution (2 molar; 1.1 eq) in 60 ml of THF p.a, andthe mixture is stirred at this temperature for 30 min.

At −15° C., a solution of 4.62 g (36 mmol; 0.66 eq) of2,2-dimethylsuccinic anhydride in 20 ml of THF p.a is then addeddropwise.

The mixture is stirred at room temperature for two hours, after which 75ml of water and 20 g of ammonium chloride are added.

The intermediate is extracted with ether and the solvents are removedunder reduced pressure. The residue is boiled under reflux with 50 g ofKOH and 165 ml of water for two days.

The mixture is cooled, acidified with concentrated HCl and extractedwith ether. The crude product is directly reacted further.

Yield: 12.20 g, 100.00% of theory. M.p. 112-115° C.

Analogously to Example XIII-1, and/or in accordance with the generalpreparation procedures, the compounds of the formula (XIII) listed inTable 31 were prepared.

TABLE 31 (XIII)

Table 31, Examples XIII Ex. No. W X Y Z A B m.p. ° C. XIII-2  H CH₃ HCH₃ —(CH₂)₅— oil XIII-3  H CH₃ CH₃ CH₃ —(CH₂)₅— oil XIII-4  CH CH₃ CH₃CH₃ —(CH₂)₅— 124-125 XIII-5  H CH₃ CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— oilXIII-6  H CH₃ H CH₃ —(CH₂)₄— oil XIII-7  H CH₃ CH₃ CH₃ —(CH₂)₄— oilXIII-8  H CH₃ Cl CH₃ —(CH₂)₅— oil XIII-9  CH H H CF₃ —(CH₂)₅— oilXIII-10 H Br CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— oil XIII-11 H CH₃ H CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— oil XIII-12 CH CH₃ CH₃ F —(CH₂)₂—CHCH₃—(CH₂)₂— oilXIII-13 H CH₃ H CH₃ —(CH₂)₃—CHCH₃—CH₂— oil XIII-14 H CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— oil XIII-15 H CH₃ Cl CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂—oil XIII-16 H CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— oil XIII-17 CH CH₃ CH₃CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— oil XIII-18 H Br CH₃ CH₃ —(CH₂)₂—O—(CH₂)₂—oil XIII-19 H Cl H CH₂CH —(CH₂)₂—O—(CH₂)₂— oil XIII-20 H CH₃ H CH₃—(CH₂)₂—O—(CH₂)₂— oil XIII-21 CH CH₃ CH₃ CH₃ —(CH₂)₂—O—(CH₂)₂— oil

Example (XIV-1)

50.0 g (0.342 mol) of 2,2-dimethylsuccinic acid are boiled under refluxin 250 ml of acetic anhydride overnight.

The mixture is filtered, concentrated using a rotary evaporator andcool-distilled twice with toluene. The residue is dissolved in a littlemethylene chloride, admixed with n-hexane, stored overnight in an icefridge, filtered off with suction and dried.

Yield: 36.40 g (83.00% of theory), oil.

¹H NMR (CDCl₃, 500 Mhz): 1.5 (s, 6H, CH₃), 2.9 (s, 2H, CH₂).

Example 1 Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound 1 part by weight ofactive compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryzae sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the green rice leaf hopper (Nephotettix cincticeps) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all leaf hoppers have been killed; 0% means that none of theleaf hoppers have been killed.

In this test, for example, the compounds of Preparation Examples Ia-2,Ia-3, Ia-4, Ia-5, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-8, I-9 and Ic-1effect, at an exemplary active compound concentration of 0.1%, a kill of100% after 6 days.

Example 2 Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the compounds of Preparation Examples Ia-1,Ib-2, Ib-4, Ib-5 and Ib-9 effect, at an exemplary active compoundconcentration of 0.1%, a kill of 100% after 7 days.

Example 3 Tetranychus Test (OP-resistant/dip Treatment)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite Tetranychus urticae are dippedinto a preparation of active compound of the desired concentration.

After the desired period of time, the effect in % is determined. 100%means that all spider mites have been killed, 0% means that none of thespider mites have been killed.

In this test, for example, the compounds of Preparation Examples Ia-2,Ia-3, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-8 and Ic-1 had, at an exemplaryactive compound concentration of 0.01%, an effect of 100% after 7 days.

Example 4 Test With Boophilus nicroplus Resistant/SP-resistant ParkhurstStrain

Test animals: Adult females which have sucked themselves full

Solvent:: Dimethyl sulphoxide

20 mg of active compound are dissolved in 1 ml of dimethyl sulphoxide,lower concentrations are prepared by dilution with the same solvent.

The test is carried out in 5 replications. 1 μl of the solution isinjected into the abdomen and the animals are transferred into dishesand kept in a controlled-environment chamber. The activity is determinedvia the inhibition of the position. 100% means that no tick hasdeposited any eggs.

In this test, for example, the compounds of Preparation Examples Ia-2and Ia-3 had, at an exemplary active compound concentration of 20μg/animal, an effect of in each case 100%.

What is claimed is:
 1. A compound of the formula (I)

wherein W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenalkyl and halogenalkoxy, each of which isunsubstituted or substituted by phenyl, phenoxy, phenylthio,phenylalkoxy or phenylalkylthio, X represents hydrogen, halogen, alkyl,alkenyl, alkinyl, alkoxy, halogenalkyl, halogenoalkoxy, cyano and nitro,each of which is unsubstituted or substituted by phenyl, phenylalkyl,phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, wherein at leastone of the substituents of W and X does not represent hydrogen, Yrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro, Z represents halogen, alkyl, alkoxy,halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or unsubstitutedor substituted phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,or Y and Z together with the carbon atoms to which they are attachedrepresent an unsubstituted or substituted ring which contains noheteroatoms, wherein X and W have the meanings mentioned above, or W andZ together with the carbon atoms to which they are attached represent anunsubstituted or substituted ring which contains no heteroatoms, whereinX and Y have the meanings mentioned above, A represents hydrogen orrepresents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representssaturated or unsaturated, unsubstituted or substituted cycloalkyl orrepresents phenyl or phenylalkyl, each of which is unsubstituted ormono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano and nitro, B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are attached form asaturated or unsaturated, unsubstituted or substituted ring which isoptionally interrupted by one or more heteroatoms, or A and B togetherwith the carbon atom to which they are attached form a ring where twosubstituents together with the carbon atoms to which they are attachedform a saturated or unsaturated ring which is unsubstituted or mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, alkyl and alkoxy and which may contain oxygen orsulphur, D¹ and D² independently of one another each represent hydrogen,halogen, unsubstituted or halogen-substituted alkyl or unsubstituted orsubstituted phenyl, G represents hydrogen (a) or represents

wherein E represents a metal ion equivalent or an ammonium ion, Irepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representsunsubstituted or substituted, saturated or unsaturated cycloalkyl whichmay be interrupted by one or more heteroatoms, or representsunsubstituted or substituted phenyl, phenylalkyl, hetaryl, orphenoxyalkyl, R² represents alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representsunsubstituted or substituted cycloalkyl, phenyl or benzyl, R³ representsalkyl which is unsubstituted or mono- or polysubstituted by identical ordifferent halogens or represents unsubstituted or substituted phenyl orphenylalkyl, R⁴ and R⁵ independently of one another each representalkyl, alkoxy, alkylamino, alkenylamino, dialkylamino, dialkenylamino,alkylthio, alkenylthio, alkinylthio, cycloalkylthio, each of which isunsubstituted or mono- or polysubstituted by identical or differenthalogens, or represent in each case unsubstituted or substituted phenyl,phenoxy or phenylthio, R⁶ and R⁷ independently of one another eachrepresent hydrogen, or represent alkyl, cycloalkyl, alkenyl, alkoxy,alkoxyalkyl, each of which is unsubstituted or mono- or polysubstitutedby identical or different halogens, or represent unsubstituted orsubstituted phenyl or unsubstituted or substituted benzyl, or togetherwith the N atom to which they are attached form an unsubstituted orsubstituted ring which optionally contains oxygen or sulphur, and anenantiomerically pure form of the compound of the formula (I), providedthat the following compounds are excluded:2-(2′,5′-dimethylphenyl)-4-methyl-1,3-cyclopentanedione and2-(2′,5′-dimethylphenyl)-4-methyl-5-isopentyl-1,3-cyclopentanedione. 2.The compound of claim 1 wherein W represents hydrogen, halogen,C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, cyano or unsubstitutedor halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio, X representshydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano, nitro orunsubstituted or halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio, wherein at least one of the substituents of Wand X does not represent hydrogen, Y represents hydrogen, halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro, Z represents halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl, cyano, nitro orunsubstituted or halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenoxy, phenylthio, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio, or Y and Z together represent unsubstituted orhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl, where X and W have the meaningsmentioned above, or W and Z together represent unsubstituted orhalogen-, C₁-C₆-alkyl-, C,-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl, where X and Y have the meaningsmentioned above, A represents hydrogen, represents unsubstituted orhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl orC₁-C₁₀-alkylthio-C₁-C₆-alkyl, or represents unsubstituted or halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or representsunsubstituted or halogen-, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenylor phenyl-C₁-C₆-alkyl, B represents C₁-C₁₂-alkyl orC₁-C₈-alkoxy-C₁-C₆-alkyl or A and B together with the carbon atom towhich they are attached represent C₃-C₁₀-cycloalkyl orC₅-C₁₀-cycloalkenyl in which optionally one methylene group is replacedby oxygen or sulphur and which are unsubstituted or substituted byC₁-C₈-alkyl, C₃-C₁₀-cycloalkyl, C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy,C₁-C₈-alkylthio, halogen or phenyl, or A and B together with the carbonatom to which they are attached represent C₅-C₈-cycloalkyl which isunsubstituted or substituted by an alkylenedioxyl or by analkylenedithioyl or by an alkylenediyl group which optionally containsone or two not directly adjacent oxygen and/or sulphur atoms and which,with the carbon atom to which it is attached, forms a further five- toeight-membered ring, or A and B together with the carbon atom to whichthey are attached represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl inwhich two carbon atoms are linked with one another by C₃-C₆-alkanediyl,C₃-C₆-alkenediyl or C₄-C₆-alkanediendiyl, each of which is unsubstitutedor substituted by C₁-C₆-alkyl, C₁-C₆-alkoxy or halogen, in which in eachcase optionally one methylene group is replaced by oxygen or sulphur, D¹and D² independently of one another each represent hydrogen, halogen,C₁-C₆-alkyl which is optionally mono- or polysubstituted by identical ordifferent halogens or represent phenyl which is unsubstituted or mono-or polysubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, nitro,C₁-C₆-halogenoalkyl or C₁-C₆-halogenoalkoxy, G represents hydrogen (a)or represents

wherein E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents unsubstituted or halogen-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl or represents unsubstituted or halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur, or represents unsubstituted orhalogen-, cyano-, nitro, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-, C₁-C₆-alkylthio- orC₁-C₆-alkylsulphonyl-substituted phenyl, or represents unsubstituted orhalogen-, nitro, cyano, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, or represents unsubstituted or halogen- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryl having one or twoheteroatoms from the group consisting of oxygen, sulphur and nitrogen,or represents unsubstituted or halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl, R² represents unsubstituted or halogen-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₂-C₈-alkyl, represents unsubstituted or halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or representsunsubstituted or halogen-, cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substituted phenyl orbenzyl, R³ represents unsubstituted or halogen-substituted C₁-C₈-alkylor unsubstituted or halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogeno-alkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of oneanother each represent in each case unsubstituted or halogen-substitutedC₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino,C₁-C₈-alkylthio or C₃-C₈-alkenylthio or represent in each caseunsubstituted or halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio and R⁶ and R⁷ independently of one another each representhydrogen, or represent unsubstituted or halogen-substituted C₁-C₈-alkyl,C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C,-alkenyl orC₁-C₈-alkoxy-C₂-C₈-alkyl, or represent unsubstituted or halogen-,C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or C₁-C₈-alkoxy-substituted phenyl orbenzyl or together represent an unsubstituted or C₁-C₆-alkyl-substitutedC₃-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur, provided that the following compound isexcluded: 2-(2′,5′-dimethylphenyl)-4-methyl-1,3-cyclopentanedione. 3.The compound of claim 1 wherein W represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro, cyano or unsubstituted or fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy orbenzyloxy, X represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano, nitro or unsubstituted or fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,benzyl or benzyloxy, wherein at least one of the substituents of W and Xdoes not represent hydrogen, Y represents hydrogen, fluorine, chlorine,bromine C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro, Z represents fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, hydroxyl, cyano or nitro or unsubstituted orfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenoxy or benzyloxy, or Y and Z together represent unsubstituted orfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl or representC₃-C₄-alkenediyl, wherein X and W have the meanings mentioned above, orW and Z together represent unsubstituted or fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₂-halogenoalkyl-substitutedC₃-C₄-alkanediyl or represent C₃-C₄-alkenediyl, wherein X and Y have themeanings mentioned above, A represents hydrogen, representsunsubstituted or fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₁-C₈-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkylor C₁-C₈-alkylthio-C₁-C₆-alkyl or represent unsubstituted or fluorine-,chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl orrepresents unsubstituted or fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl orphenyl-C₁-C₄-alkyl, B represents C₁-C₁₀-alkyl orC₁-C₆-alkoxy-C₁-C₄-alkyl or A and B together with the carbon atom towhich they are attached represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenylin which in each case optionally one methylene group is replaced byoxygen or sulphur and which are unsubstituted or substituted byC₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, fluorine, chlorine or phenyl, or A and B together withthe carbon atom to which they are attached represent C₅-C₈-cycloalkylwhich is substituted by an alkylenedioxyl or by an alkylenedithio groupor by an alkylenediyl group which optionally contains one or two notdirectly adjacent oxygen or sulphur atoms which, with the carbon atom towhich it is attached, forms a further five- to seven-membered ring, or Aand B together with the carbon atom to which they are attached representC₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which two carbon atoms arelinked by unsubstituted or C₁-C₄-alkyl-, C₁-C₄-alkoxy-, fluorine-,chlorine- or bromine-substituted C₃-C₅-alkanediyl, C₃-C₅-alkenediyl,where in each case optionally one methylene group is replaced by oxygenor sulphur, or by butadienediyl, D¹ and D² independently of one anothereach represent hydrogen or represent C₁-C₄-alkyl which is unsubstitutedor mono- to pentasubstituted by identical or different substituents fromthe group consisting of fluorine and chlorine, G represents hydrogen (a)or represents one of the groups

wherein E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents unsubstituted or fluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl or poly-C₁-C₆-alkoxy-C₁-C₆-alkyl orrepresents unsubstituted or fluorine-, chlorine- C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally one or twonot directly adjacent methylene groups are replaced by oxygen and/orsulphur, or represents unsubstituted or fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl, or represents unsubstituted orfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl-C₁-C₄-alkyl, or represents unsubstituted or fluorine-, chlorine-bromine- or C₁-C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl,pyrimidyl, furanyl or thienyl, or represents unsubstituted or fluorine-,chlorine-, bromine- or C₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl, R²represents unsubstituted or fluorine- or chlorine-substitutedC₁-C₁₆-alkyl, C₂-c₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₂-C₆-alkyl, or represents unsubstituted or fluorine-,chlorine-, C₁-C₄-alkyl- or C₁-C₄alkoxy-substituted C₃-C₇-cycloalkyl orrepresents unsubstituted or fluorine-, chlorine, bromine-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl or benzyl, R³ representsunsubstituted or fluorine- or chlorine-substituted C₁-C₆-alkyl orrepresents unsubstituted or fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkoxy-,C₁-C₂-halogenoalkyl-, cyano or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent in each caseunsubstituted or fluorine- or chlorine-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthioor C₃-C₄-alkenylthio or represent unsubstituted or fluorine-, chlorine-,bromine-, nitro-, cyano-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-,C₁-C₃-alkylthio-, C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl- orC₁-C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio and R⁶ andR⁷ independently of one another each represent hydrogen, or representunsubstituted or fluorine- or chlorine-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, or represent unsubstituted or fluorine-,chlorine-, bromine-, C₁-C₅-halogenoalkyl-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted phenyl or benzyl, or together represent anunsubstituted or C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in whichoptionally one methylene group is replaced by oxygen or sulphur,provided that the following compound is excluded:2-(2′,5′-dimethylphenyl)-4-methyl-1,3-cyclopentanedione.
 4. The compoundof claim 1, wherein W represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, tert-butyl,methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano, nitro, phenyl or benzyloxy, Xrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,n-propyl, n-butyl, iso-butyl, iso-propyl, tert-butyl, methoxy, ethoxy,n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano, nitro, phenyl or benzyloxy, wherein at least oneof the substituents of W and X does not represent hydrogen, Y representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl,iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy,iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyanoor nitro, Z represents fluorine, chlorine, bromine, methyl, ethyl,n-propyl, n-butyl, iso-butyl, iso-propyl, tert-butyl, methoxy, ethoxy,n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano or nitro, or Y and Z together representunsubstituted or fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,iso-propyl-, methoxy-, ethoxy-, n-propoxy-, iso-propoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl, wherein W and X have themeanings mentioned above, or W and Z together represent unsubstituted orfluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-,ethoxy-, n-propoxy-, iso-propoxy- or trifluoromethyl-substitutedC₃-C₄-alkanediyl, wherein X and Y have the meanings mentioned above, Arepresents hydrogen, or represents unsubstituted or fluorine- orchlorine-substituted C₁-C₈-alkyl, C₃-C₄-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl orC₁-C₆-alkylthio-C₁-C₄-alkyl or represents unsubstituted or fluorine-,chlorine-, methyl- or methoxy-substituted C₃-C₆-cycloalkyl or representsunsubstituted or fluorine-, chlorine-, bromine-, methyl-, ethyl-,n-propyl-, iso-propyl-, methoxy-, ethoxy-, trifluoromethyl-,trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl, Brepresents C₁-C₈-alkyl or C₁-C₄-alkoxy-C₁-C₂-alkyl or A and B togetherwith the carbon atom to which they are attached representC₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which in each case optionallyone methylene group is replaced by oxygen or sulphur and which areunsubstituted or substituted by methyl, ethyl, n-propyl, iso-propyl,n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl,methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy,sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine, chlorine orphenyl, D¹ and D² independently of one another each represent hydrogen,methyl or ethyl, G represents hydrogen (a) or

wherein E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents unsubstituted or fluorine- or chlorine-substitutedC₁-C₁₄-alkyl, C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,C₁-C₄-alkylthio-C₁-C₆-alkyl or poly-C₁-C₄-alkoxy-C₁-C₄-alkyl orrepresents unsubstituted or fluorine-, chlorine-, methyl-, ethyl-,n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-, methoxy-,ethoxy-, n-propoxy- or iso-propoxy-substituted C₃-C₆-cycloalkyl in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur, or represents unsubstituted orfluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-,trifluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- orethylsulphonyl-substituted phenyl, or represents unsubstituted orfluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-,methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substitutedbenzyl, or represents unsubstituted or fluorine-, chlorine-, bromine-,methyl- or ethyl-substituted furanyl, thienyl or pyridyl, or representsunsubstituted or fluorine-, chlorine-, methyl- or ethyl-substitutedphenoxy-C₁-C₄-alkyl, R² represents unsubstituted or fluorine- orchlorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl, or representsunsubstituted or fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,iso-propyl- or methoxy-substituted C₃-C₆-cycloalkyl, or representsunsubstituted or fluorine-, chlorine-, cyano- nitro-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl, R³ representsunsubstituted or fluorine-, or chlorine-substituted methyl, ethyl,n-propyl, iso-propyl, n-butyl, tert-butyl or unsubstituted or fluorine-,chlorine-, bromine-, methyl-, ethyl-, iso-propyl-, tert-butyl-,methoxy-, ethoxy-, iso-propoxy-, trifluoromethyl-, trifluoromethoxy-,cyano- or nitro-substituted phenyl or benzyl, R⁴ and R⁵ independently ofone another each represent unsubstituted or fluorine- orchlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio or represent unsubstituted orfluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl, phenoxy orphenylthio and R⁶ and R⁷ independently of one another each representhydrogen, or represent unsubstituted or fluorine- orchlorine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, represent unsubstituted orfluorine-, chlorine-, bromine-, methyl-, methoxy- ortrifluoromethyl-substituted phenyl or benzyl or together represent anunsubstituted or methyl- or ethyl-substituted C₅-C₆-alkylene radical inwhich optionally one methylene group is replaced by oxygen or sulphur,provided that the following compound is excluded:2-(2′,5′-dimethylphenyl)-4-methyl-1,3-cyclopentanedione.
 5. A compoundof the formula (II)

wherein W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenalkyl and halogenalkoxy, each of which isunsubstituted or substituted by phenyl, phenoxy, phenylthio,phenylalkoxy or phenylalkylthio, X represents hydrogen, halogen, alkyl,alkenyl, alkinyl, alkoxy, halogenalkyl, halogenoalkoxy, cyano and nitro,each of which is unsubstituted or substituted by phenyl, phenylalkyl,phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, wherein at leastone of the substituents of W and X does not represent hydrogen, Yrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro, Z represents halogen, alkyl, alkoxy,halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or unsubstitutedor substituted phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,or Y and Z together with the carbon atoms to which they are attachedrepresent an unsubstituted or substituted ring which contains noheteroatoms, wherein X and W have the meanings mentioned above, or W andZ together with the carbon atoms to which they are attached represent anunsubstituted or substituted ring which contains no heteroatoms, whereinX and Y have the meanings mentioned above, A represents hydrogen orrepresents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representssaturated or unsaturated, unsubstituted or substituted cycloalkyl orrepresents phenyl or phenylalkyl, each of which is unsubstituted ormono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano and nitro, B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are attached form asaturated or unsaturated, unsubstituted or substituted ring which isoptionally interrupted by one or more heteroatoms, or A and B togetherwith the carbon atom to which they are attached form a ring where twosubstituents together with the carbon atoms to which they are attachedform a saturated or unsaturated ring which is unsubstituted or mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, alkyl and alkoxy and which may contain oxygen orsulphur, D¹ and D² independently of one another each represent hydrogen,halogen, unsubstituted or halogen-substituted alkyl or unsubstituted orsubstituted phenyl, and R⁸ represents alkyl.
 6. A compound of theformula (XIII)

wherein W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenalkyl and halogenalkoxy, each of which isunsubstituted or substituted by phenyl, phenoxy, phenylthio,phenylalkoxy or phenylalkylthio, X represents hydrogen, halogen, alkyl,alkenyl, alkinyl, alkoxy, halogenalkyl, halogenoalkoxy, cyano and nitro,each of which is unsubstituted or substituted by phenyl, phenylalkyl,phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, wherein at leastone of the substituents of W and X does not represent hydrogen, Yrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro, Z represents halogen, alkyl, alkoxy,halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or unsubstitutedor substituted phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,or Y and Z together with the carbon atoms to which they are attachedrepresent an unsubstituted or substituted ring which contains noheteroatoms, wherein X and W have the meanings mentioned above, or W andZ together with the carbon atoms to which they are attached represent anunsubstituted or substituted ring which contains no heteroatoms, whereinX and Y have the meanings mentioned above, A represents hydrogen orrepresents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representssaturated or unsaturated, unsubstituted or substituted cycloalkyl orrepresents phenyl or phenylalkyl, each of which is unsubstituted ormono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano and nitro, B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are attached form asaturated or unsaturated, unsubstituted or substituted ring which isoptionally interrupted by one or more heteroatoms, or A and B togetherwith the carbon atom to which they are attached form a ring where twosubstituents together with the carbon atoms to which they are attachedform a saturated or unsaturated ring which is unsubstituted or mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, alkyl and alkoxy and which may contain oxygen orsulphur, D¹ and D² independently of one another each represent hydrogen,halogen, unsubstituted or halogen-substituted alkyl or unsubstituted orsubstituted phenyl.
 7. A compound of the formula (XVI)

wherein W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenalkyl and halogenalkoxy, each of which isunsubstituted or substituted by phenyl, phenoxy, phenylthio,phenylalkoxy or phenylalkylthio, X represents hydrogen, halogen, alkyl,alkenyl, alkinyl, alkoxy, halogenalkyl, halogenoalkoxy, cyano and nitro,each of which is unsubstituted or substituted by phenyl, phenylalkyl,phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, wherein at leastone of the substituents of W and X does not represent hydrogen, Yrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro, Z represents halogen, alkyl, alkoxy,halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or unsubstitutedor substituted phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,or Y and Z together with the carbon atoms to which they are attachedrepresent an unsubstituted or substituted ring which contains noheteroatoms, wherein X and W have the meanings mentioned above, or W andZ together with the carbon atoms to which they are attached represent anunsubstituted or substituted ring which contains no heteroatoms, whereinX and Y have the meanings mentioned above, A represents hydrogen orrepresents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, each of which is unsubstituted or mono- orpolysubstituted by identical or different halogens, or representssaturated or unsaturated, unsubstituted or substituted cycloalkyl orrepresents phenyl or phenylalkyl, each of which is unsubstituted ormono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano and nitro, B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are attached form asaturated or unsaturated, unsubstituted or substituted ring which isoptionally interrupted by one or more heteroatoms, or A and B togetherwith the carbon atom to which they are attached form a ring where twosubstituents together with the carbon atoms to which they are attachedform a saturated or unsaturated ring which is unsubstituted or mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, alkyl and alkoxy and which may contain oxygen orsulphur, D¹ and D² independently of one another each represent hydrogen,halogen, unsubstituted or halogen-substituted alkyl or unsubstituted orsubstituted phenyl, and R⁸ and R^(8′) each represent alkyl.
 8. A processfor preparing a compound of the formula (I) according to claim 1,comprising the steps of: a) intermolecularly cyclizing a compound of theformula (II)

wherein A, B, D¹, D², W, X, Y and Z are each as defined in claim 1, andR⁸ represents alkyl, producing a compound of the formula (Ia)

b) reacting the compound of the formula (Ia) with an acyl halide of theformula (III)

wherein R₁ is as defined in claim 1, and Hal represents halogen, or c)reacting the compound of the formula (Ia) with a carboxylic anhydride ofthe formula (IV) R¹—CO—O—CO—R¹  (IV) wherein R¹ is as defined in claim1, or d) reacting the compound of the formula (Ia) with a chloroformicester or a chloroformic thioester of the formula (V) R²—M—CO—Cl  (V)wherein R² and M are each as defined in claim 1, or e) reacting thecompound of the formula (Ia) with a chloromonothioformic ester or achlorodithioformic ester of the formula (VI)

wherein R² and M are each as defined in claim 1, or f) reacting thecompound of the formula (Ia) with a sulphonyl chloride of the formula(VII) R³—SO₂—Cl  (VII) wherein R³ is as defined in claim 1, or g)reacting the compound of the formula (Ia) with a phosphorus compound ofthe formula (VIII)

wherein L, R⁴ and R⁵ are each as defined in claim 1, and Hal representshalogen, or h) reacting the compound of the formula (Ia) with anisocyanate or an isothiocyanate of the formula (XI) R⁶—N═C═L  (XI)wherein R⁶ and L are each as defined in claim 1, or i) reacting thecompound of the formula (Ia) with a carbamoyl chloride or thiocarbamoylchloride of the formula (XII)

wherein L, R⁶ and R⁷ are each as defined in claim 1, or j) reacting thecompound of the formula (Ia) with a metal compound of the formula (IX)Me(OR¹⁰)_(t)  (IX) wherein Me represents a mono- or divalent metal, trepresents the number 1 or 2, and R¹⁰ represents hydrogen or alkyl, ork) reacting the compound of the formula (Ia) with an amine of theformula

wherein R¹⁰, R¹¹ and R¹² each represent hydrogen or alkyl.
 9. Theprocess of claim 8 wherein the reaction in step a) is carried out in thepresence of a diluent and a base.
 10. The process of claim 8 wherein thereaction in steps b), c), d), e), f), g), h), i), j) and k) are carriedout in the presence of a diluent.
 11. The process of claim 8 wherein thereaction in steps b), c), d), e), f), g) and i) are carried out in thepresence of an acid binder.
 12. The process of claim 8 wherein thereaction in steps b), c), d), e), f), g) and i) are carried out in thepresence of a diluent and an acid binder.
 13. The process of claim 8wherein the reaction in step h) is carried out in the presence of acatalyst.
 14. The process of claim 8 wherein the reaction in step h) iscarried out the presence of a diluent and a catalyst.
 15. A pesticide orherbicide composition comprising an effective amount of one or morecompounds of claim 1 and a member selected from the group consisting ofa solvent, an emulsifier, a dispresant, a binder, a water repellent, adesiccant, a UV stabilizer, a colorant and mixtures thereof.
 16. Amethod for controlling pests and weeds, comprising the step of allowingan effective amount of one or more compound of claim 1 to act on pestsor weeds and/or their habitat.
 17. A process for preparing a pesticideor a herbicide comprising mixing a compound of claim 1 with a memberselected from the group consisting of a solvent, an emulsifier, adispresant, a binder, a water repellent, a desiccant, a UV stabilizer, acolorant and mixtures thereof.